α-D-glucopyranosyl-(1-3)-α-D-mannopyranosyl-(1-7)-4-methylumbelliferone | 325484-29-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: α-D-glucopyranosyl-(1-3)-α-D-mannopyranosyl-(1-7)-4-methylumbelliferone
• 英文别名: 4-methylumbelliferyl (α-D-glucopyranosyl)-(1→3)-α-D-mannopyranoside；7-[(2R,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methylchromen-2-one
• CAS: 325484-29-5
• 化学式: C₂₂H₂₈O₁₃
• 分子量: 500.457
• InChiKey: JNAWLDYZIIXRCJ-WZBDZHSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  205
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  α-D-glucopyranosyl-(1-3)-α-D-mannopyranosyl-(1-7)-4-methylumbelliferone 在 1-脱氧野尻霉素 phosphate buffer 、 rat liver Golgi protein containing endo-α-1,2-mannosidase 、 Triton X-100 作用下， 以 水 为溶剂， 反应 2.0h， 生成 羟甲香豆素 、 α-D-glucopyranosyl-(1-3)-D-mannopyranose
  参考文献：
  名称：

  Synthesis of α-D-Glucopyranosyl-(1-3)-α-D-Mannopyranosyl-(1-7)-4-Methylumbelliferone, A Fluorogenic Substrate for Endo-α-1,2-Mannosidase

  摘要：

  alpha -D-Glucopyranosyl-(1-3)-alpha -D-mannopyranosyl-(1-7)-4-methylumbelliferone (Glc-Man-Muf) was synthesized as a potential fluorogenic substrate for endo-alpha -1,2-mannosidase. The synthesis was designed in a convergent way. The glucose donor ethyl 2,3,4,6-tetra-O-benzyl-1-thio-beta -glucopyranoside and the mannose acceptor 1,2:4,6-di-O-isopropylidene-beta -mannopyranose were coupled in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid to yield the corresponding disaccharide derivative. After conversion into peracetylated alpha -D-glucopyranosyl-(1-3)-alpha -D-mannopyranose the disaccharide was attached to 4-methylumbelliferone using the Helferich method. After separation of the desired isomer, deacetylation yielded the title compound. Glc-Man-Muf was used as st substrate in endomannosidase assays with rat liver Golgi preparations as an enzyme source (in the presence of the alpha -glucosidase inhibitor deoxynojirimycin). The degradation of Glc-Man-Muf was linear with protein up to 300 mug and with time up to 2 h. V-max and K-m were determined to be 0.17 nmol/mg x h and 3.7 mM, respectively.

  DOI：

  10.1080/07328300008544148
• 作为产物：
  描述：

  α/β-D-glucopyranosyl-(1-3)-1,2,4,6-tetra-O-acetyl-α-D-mannopyranose 在 吡啶 、 sodium methylate 、 zinc(II) chloride 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 146.0h， 生成 α-D-glucopyranosyl-(1-3)-α-D-mannopyranosyl-(1-7)-4-methylumbelliferone
  参考文献：
  名称：

  Synthesis of α-D-Glucopyranosyl-(1-3)-α-D-Mannopyranosyl-(1-7)-4-Methylumbelliferone, A Fluorogenic Substrate for Endo-α-1,2-Mannosidase

  摘要：

  alpha -D-Glucopyranosyl-(1-3)-alpha -D-mannopyranosyl-(1-7)-4-methylumbelliferone (Glc-Man-Muf) was synthesized as a potential fluorogenic substrate for endo-alpha -1,2-mannosidase. The synthesis was designed in a convergent way. The glucose donor ethyl 2,3,4,6-tetra-O-benzyl-1-thio-beta -glucopyranoside and the mannose acceptor 1,2:4,6-di-O-isopropylidene-beta -mannopyranose were coupled in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid to yield the corresponding disaccharide derivative. After conversion into peracetylated alpha -D-glucopyranosyl-(1-3)-alpha -D-mannopyranose the disaccharide was attached to 4-methylumbelliferone using the Helferich method. After separation of the desired isomer, deacetylation yielded the title compound. Glc-Man-Muf was used as st substrate in endomannosidase assays with rat liver Golgi preparations as an enzyme source (in the presence of the alpha -glucosidase inhibitor deoxynojirimycin). The degradation of Glc-Man-Muf was linear with protein up to 300 mug and with time up to 2 h. V-max and K-m were determined to be 0.17 nmol/mg x h and 3.7 mM, respectively.

  DOI：

  10.1080/07328300008544148

文献信息

• Structural and Kinetic Dissection of the<i>endo</i>-α-1,2-Mannanase Activity of Bacterial GH99 Glycoside Hydrolases from<i>Bacteroides</i> spp.
  作者：Zalihe Hakki、Andrew J. Thompson、Stephanie Bellmaine、Gaetano Speciale、Gideon J. Davies、Spencer J. Williams

  DOI：10.1002/chem.201405539

  日期：2015.1.26

  Glycoside hydrolase family 99 (GH99) was created to categorize sequence‐related glycosidases possessing endo‐α‐mannosidase activity: the cleavage of mannosidic linkages within eukaryotic N‐glycan precursors (Glc1–3Man9GlcNAc2), releasing mono‐, di‐ and triglucosylated‐mannose (Glc1–3‐1,3‐Man). GH99 family members have recently been implicated in the ability of Bacteroides spp., present within the gut

  糖苷水解酶家族99（GH99）的创建是为了对具有内切α-甘露糖苷酶活性的序列相关糖苷酶进行分类：真核N-聚糖前体（Glc 1-3 Man 9 GlcNAc 2）中甘露糖苷键的裂解，释放单，双-和triglucosylated甘露糖（GLC 1-3 -1,3-曼）。GH99家族成员最近与拟杆菌的能力有关 spp.spp。，存在于肠道菌群内，通过分解分支内的αMan-1,3-αMan→1,2-αMan-1,2-αMan序列来代谢真菌细胞壁α-甘露聚糖，从而释放α-1,3-甘露二糖偏离主要的α-1,6-甘露聚糖骨架。我们报告了一系列底物和抑制剂的开发，我们将其用于在动力学和结构上表征细菌拟南芥（Theactotaides thetaiotaomicron）和xylanisolvens的细菌GH99酶的这种新型内-α-1,2-甘露聚糖酶活性。这些数据表明大约为5 kJ mol -1对-2子位点中相